Stereoselective Gridization of Ladder-Type Grids with Four Chiral Centers
Yang Li , Yueting Pu , Zheng Zhang , Fangju Tao , Xiaoyan Li , Jingrui Zhang , Xin Chen , Yuezheng Gao , Ying Wei , Linghai Xie
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (24) : 3343 -3348.
Stereoselective Gridization of Ladder-Type Grids with Four Chiral Centers
Comprehensive Summary:To address the stereoselective synthesis challenge in π-stacked grids with four chiral centers, we utilized coplanar and highly rigid 11, 12-dihydroindeno[2, 1- a]fluorene-11, 12-diol and 2, 2’-bithiophene as synthons, employing Friedel-Crafts gridization (FCG). Leveraging the supramolecular interactions of S···S and π···π within the thiophene moiety, along with the steric effect of the 11, 12-dihydroindeno[2, 1- a]fluorene scaffold, we successfully achieved the exclusive generation of a single isomer of Ladder-type π-stacked grids (LGs-IF) containing six theoretical isomers. By subsequently substituting 2, 2’-bithiophene with thiophene/bithiophene derivatives as synthons, we maintained an exceptionally high level of stereoselectivity. This study introduces a novel approach for the stereo-controlled preparation of grids involving multi-chiral centers.
Stereoselectivity / Diastereoselectivity / C–C coupling / Friedel-Crafts gridization / Macrocycles / Four chiral centers / Supramolecular interactions / Steric effect
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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